CN101468949A - Antineoplastic novel compound in immature exocarpof Juglans mandshurica Maxim, method for determining content thereof and use - Google Patents
Antineoplastic novel compound in immature exocarpof Juglans mandshurica Maxim, method for determining content thereof and use Download PDFInfo
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Abstract
The invention relates to a novel anti-tumor compound in north Juglans regia and a content assay method and application thereof. The prior method does not contain a method for measuring the content of anti-tumor effective ingredients of the north Juglans regia, so that the method can not effectively control the mass of medicines and preparation and does not have specificity, accuracy and reliability. The invention utilizes high-performance liquid chromatography to establish the content assay method which takes the novel anti-tumor compound in the north Juglans regia as a target. The structural formula of the novel compound is the right formula (I). The novel anti-tumor compound is measured by the HPLC method, and is applied in the field of medicine.
Description
Technical field:
The present invention relates to antineoplastic novel compound and content assaying method thereof in a kind of immature exocarp of Juglans mandshurica Maxim.
Background technology:
Cancer is the serious disease that threatens the human life, and therefore, the research of cancer therapy drug is the focus of World Focusing always.Chinese medicine is antitumor to have distinctive feature at the chemicals that compares aspect raising immunizing power and the reduction mutagenesis toxicity, therefore, from motherland's medicine treasure-house, seek the antitumor Chinese medicine of determined curative effect, clear and definite its effective substance, and then develop the new drug of high-efficiency low-toxicity, become the focus that tcm field is studied for many years.
Immature exocarp of Juglans mandshurica Maxim is the immature fruit of juglandaceae plant Juglans mandshurica (Juglans Mandshurica MAXIM.), abounds with in each county, outskirts of a town, northeast, at the anodyne that is commonly used for the various cancers of treatment and tetter and various pain among the people.Immature exocarp of Juglans mandshurica Maxim recorded and became a kind of Chinese medicine in Heilongjiang Province's medicinal material standard and be applied to clinical and produce calendar year 2001.Alimentary tract cancers such as the crude extract preparation for treating cancer of the stomach of immature exocarp of Juglans mandshurica Maxim, the esophageal carcinoma, have the case of two more than ten years treatment observation to prove (Li Zhongyuan. the 120 routine clinical observations of Exocarpium Juglandis Immaturum treatment carcinoma of esophago cardia. Chinese materia medica information, 1988, (3): 3), its antitumor action is unquestionable.Yet its effective substance research does not deeply launch, bibliographical information rests on the pharmacological action of its crude extract more and (Ji Yubin is gone up in the antitumor action research that lacks its effective constituent, the horse grand plan, Yang Bo, draw the cutting edge of a knife or a sword in morning. the antitumor action research of the different extract parts of immature exocarp of Juglans mandshurica Maxim. herbal medicine, 2004,35 (10): 1145-1147), thereby the serious hysteresis that causes this medicine resource of immature exocarp of Juglans mandshurica Maxim to be developed.
Do not have the antitumor content of effective measuring method of immature exocarp of Juglans mandshurica Maxim in the existing method, therefore can not more effectively control the quality of medicinal material and preparation, do not have specificity, accuracy and reliability.It is the content assaying method of index that the present invention utilizes high performance liquid chromatography to set up with the antineoplastic novel compound in the immature exocarp of Juglans mandshurica Maxim, and the guarantee of science is provided in antitumor application for immature exocarp of Juglans mandshurica Maxim.
Summary of the invention:
The purpose of this invention is to provide antineoplastic novel compound and content assaying method and application in a kind of immature exocarp of Juglans mandshurica Maxim.
Above-mentioned purpose realizes by following technical scheme:
Antineoplastic novel compound in the immature exocarp of Juglans mandshurica Maxim, the plain A of called after Exocarpium Juglandis Immaturum, described All new compounds formula is:
The content assaying method of antineoplastic novel compound in the described immature exocarp of Juglans mandshurica Maxim, adopt the HPLC method to measure, get the plain A reference substance of Exocarpium Juglandis Immaturum, the accurate title, decide, and adds methyl alcohol and make the solution that every 1ml contains 0.2mg, product solution in contrast, got the immature exocarp of Juglans mandshurica Maxim powder 1g of No. three sieves, the accurate title, decide, and adds 50% methyl alcohol supersound process 30 minutes, put cold, claim again to decide weight, supply the weight that subtracts mistake, shake up with 50% methyl alcohol, filter, as need testing solution, accurate respectively reference substance solution and each 10 μ l of need testing solution of drawing inject liquid chromatograph, measure, promptly.
The content assaying method of the antineoplastic novel compound in described a kind of immature exocarp of Juglans mandshurica Maxim, adopt the HPLC method to measure, be meant that chromatographic condition is to adopt octadecylsilane chemically bonded silica as weighting agent, moving phase is that the volume ratio of 0.25% Glacial acetic acid (V/V) and methyl alcohol is 25:75, the detection wavelength is 350nm, column temperature is 30 ℃, and number of theoretical plate calculates by the plain A of Exocarpium Juglandis Immaturum peak and is not less than 3000.
The application of antineoplastic novel compound in the described immature exocarp of Juglans mandshurica Maxim in the preparation antitumor drug.
This technical scheme has following beneficial effect:
1. we are in the research at the antitumor effective constituent of immature exocarp of Juglans mandshurica Maxim, detect the method that combines through extraction, separation and purification with cytoactive, finally obtained to have a new compound of anti-tumor activity, the plain A (qinglongyitin A) of called after Exocarpium Juglandis Immaturum, and adopt mass spectrum and high resolution NMR technology, determined the structure of this compound.
The invention provides a kind of compound of not reporting with antitumor action, by to cancer cells inhibition test and pharmacodynamics test, proved that this compound has good antitumour activity, can make the antitumor drug that is suitable for clinical use with drug excipient.This compound is to people HL-60 leukemia cell, people Kato-III stomach cancer cell and people A
549Lung carcinoma cell has significant inhibitory effect, and the transplanted tumor in nude mice model research has proved that also this compound is to liver cancer cell H
22Growth has the obvious suppression effect, and can obviously prolong the mouse survival time, has good antitumor action.
The Chinese medicine and the quality of the pharmaceutical preparations thereof stable and controlled be the bottleneck of the modernization of Chinese medicine always, this compound is one of effective constituent of Chinese medicine immature exocarp of Juglans mandshurica Maxim, can be used as the index of the immature exocarp of Juglans mandshurica Maxim medicinal material and the quality of the pharmaceutical preparations thereof control, setting up with this composition on this basis is the discriminating of index and the quality control standard of assay project, realize the stable and controlled of the immature exocarp of Juglans mandshurica Maxim medicinal material and the quality of the pharmaceutical preparations thereof, this compound will be extensive use of as the Chinese medicine reference substance.
3. what the present invention set up is the quality that the content assaying method of index can be controlled the immature exocarp of Juglans mandshurica Maxim medicinal material effectively with this compound, has more specificity, accuracy and reliability than existing quality standard.This compound has good antitumour activity, is index with this new compound, the content assaying method that adopts high performance liquid chromatography to set up, simple and easy to do, favorable reproducibility can more effectively be controlled the quality of medicinal material and preparation, has specificity, accuracy and reliability.
Description of drawings:
Accompanying drawing 1 is The compounds of this invention (I)
1H-
1Observed structure iron in the H COSY spectrum.
Accompanying drawing 3 is typical curves of the plain A assay of Exocarpium Juglandis Immaturum.
The specific embodiment of the present invention:
Embodiment 1:
Antineoplastic novel compound in the immature exocarp of Juglans mandshurica Maxim, the plain A of called after Exocarpium Juglandis Immaturum, described All new compounds formula is:
The content assaying method of antineoplastic novel compound in the described immature exocarp of Juglans mandshurica Maxim, adopt the HPLC method to measure, get the plain A reference substance of Exocarpium Juglandis Immaturum, the accurate title, decide, and adds methyl alcohol and make the solution that every 1ml contains 0.2mg, product solution in contrast, got the immature exocarp of Juglans mandshurica Maxim powder 1g of No. three sieves, the accurate title, decide, and adds 50% methyl alcohol supersound process 30 minutes, put cold, claim again to decide weight, supply the weight that subtracts mistake, shake up with 50% methyl alcohol, filter, as need testing solution, accurate respectively reference substance solution and each 10 μ l of need testing solution of drawing inject liquid chromatograph, measure, promptly.
The content assaying method of the antineoplastic novel compound in described a kind of immature exocarp of Juglans mandshurica Maxim, adopt the HPLC method to measure, be meant that chromatographic condition is to adopt octadecylsilane chemically bonded silica as weighting agent, moving phase is that the volume ratio of 0.25% Glacial acetic acid (V/V) and methyl alcohol is 25:75, the detection wavelength is 350nm, column temperature is 30 ℃, and number of theoretical plate calculates by the plain A of Exocarpium Juglandis Immaturum peak and is not less than 3000.
The application of antineoplastic novel compound in the described immature exocarp of Juglans mandshurica Maxim in the preparation antitumor drug.
Embodiment 2:
The content assaying method of the antineoplastic novel compound in the immature exocarp of Juglans mandshurica Maxim, adopt the HPLC method to measure, chromatographic condition is for adopting octadecylsilane chemically bonded silica as weighting agent, and moving phase is that the volume ratio of 0.25% Glacial acetic acid (V/V) and methyl alcohol is 25:75, the detection wavelength is 350nm, column temperature is 30 ℃, and number of theoretical plate calculates by the plain A of Exocarpium Juglandis Immaturum peak and is not less than 3000, and it is an amount of to get the plain A reference substance of Exocarpium Juglandis Immaturum, the accurate title, decide, add methyl alcohol and make the solution that every 1ml contains 0.2mg, product solution was got the immature exocarp of Juglans mandshurica Maxim powder 1g that sieves for No. three in contrast, the accurate title, decide, add 50% methyl alcohol supersound process 30 minutes, put coldly, claim to decide weight again, supply the weight that subtracts mistake with 50% methyl alcohol, shake up, filter, as need testing solution, accurate respectively reference substance solution and each 10 μ l of need testing solution of drawing, inject liquid chromatograph, measure, promptly.
Embodiment 3:
The preparation of the antineoplastic novel compound in the immature exocarp of Juglans mandshurica Maxim
The material source immature exocarp of Juglans mandshurica Maxim is the immature fruit of juglandaceae plant Juglans mandshurica (Juglans MandshuricaMAXIM.), adopts in 5 constant virtues, Heilongjiang Province county mid-July, and the herbarium sample is concealed in Chinese herbal medicine specimen shop, institute for drug control, Heilongjiang Province.
Extract and separate fresh immature exocarp of Juglans mandshurica Maxim with one week of 75% alcohol immersion, extract altogether three times, united extraction liquid, concentrating under reduced pressure, be concentrated into the concentrated solution of relative density 1.10-1.14 (50 ℃), concentrated solution adds 10 times of water gagings and disperses, centrifugal, get supernatant liquor, inject the Diaion HP-20 macroporous adsorbent resin of having handled well (ratio of concentrated solution and resin is 1:50), flow velocity 10ml/min, respectively with the washing of 3 times of column volumes, 30% ethanol of 5 times of column volumes is washed, and collects 30% ethanol eluate, and the elutriant evaporated under reduced pressure obtains residue, residue dissolves with small amount of methanol, filter, filtrate is injected (column diameter 2cm, column length 2m on the sephadex lh-20 post, applied sample amount is a 1g residue/each), with methanol-eluted fractions, flow velocity 1.0ml/min, elutriant carry out thin-layer chromatography on silica-gel plate, developping agent is chloroform-methanol (84:16), merges R
fValue is 0.3 one-component, must this compound with recrystallizing methanol, and purity is more than 98%.
The physico-chemical property of the plain A of Exocarpium Juglandis Immaturum:
The plain A of Exocarpium Juglandis Immaturum is an amorphous powder.IR(KBr)ν
max：3414，2924，2857，2372，1618，1456，1391，1263，1116，618。UV(MeOH)λ
max(logε)：209nm(3.52)，263nm(3.92)，344nm(4.41)。[α]
D 25-21°(c＝0.1，MeOH)。
1H-NMR (500MHz, CD
3OD) and
13C-NMR (125MHz, CD
3OD) the spectrum data see Table 1.ESI-MS (positive) m/z 379.1[M+Na]; HR-FAB-MS (positive) m/z379.1002[M+Na] (calculated value C
19H
16O
7Na 379.1005).
The plain A's of Exocarpium Juglandis Immaturum
1Show five fragrant protons in the H-NMR spectrum, at δ 6.67 (1H, dd, J=8.2,1.1), δ 7.42 (1H, dd, J=8.2,7.8), δ 7.29 (1H, dd, J=7.8,1.1) be a cover ABC coupling system, δ 6.53 (1H, s), (1H s) is the aroma system that a cover contraposition hydrogen replaces to δ 7.06, at high field region δ 2.50 (1H, dd, J=12.4,4.2), δ 2.57 (1H, dd, J=12.4,1.8) be that a methylene radical and a methyne are at δ 3.15 (1H, d, J=4.2,1.8) the ortho position coupling, its excess-three proton is respectively at δ 3.31 (1H, m) and δ 2.68 (2H, m) ortho position coupling, these
1H-
1Obtain conclusive evidence (seeing accompanying drawing 1) in the H COSY spectrum.
13C-NMR spectrum composes as can be known in conjunction with HMQC that δ 208.7 is carbonyl carbon, is respectively a methylene radical and a methyne at δ 48.9 and δ 36.7, and δ 70.9 is for being connected with the tertiary carbon of hydroxyl.δ 2.50 (H-3) in the HMBC spectrum, the methylene radical of δ 2.57 (H-3) is relevant with δ 208.7 (C-1) carbonyl, and the methyne of δ 3.15 (H-2) is relevant with δ 70.9 (C-4), can infer and contain the Tetralone an intermediate of Sertraline structure in the molecule.δ 6.67 (H-5) is relevant with δ 70.9 (C-4) in the HMBC spectrum has also proved this point, and shows that the phenyl ring in the Tetralone an intermediate of Sertraline is an ABC coupling system.An other cover aroma system is to be connected on the δ 70.9 (C-4), and this can observe the relevant peaks of δ 7.06 (H-5 ') and δ 70.9 (C-4) in HMBC spectrum.δ 3.31 in HMBC spectrum (H-7 ') and δ 116.1 (C-2 ') are relevant, and δ 6.53 (H-2 ') and δ 40.3 (C-7 ') are relevant, show that δ 40.3 (C-7 ') and δ 45.6 (C-8 ') are connected on another phenyl ring.Wherein δ 2.68 (H-8 ') is long-range relevant with 48.9 (C-2), δ 3.31 (H-7 ') long-range relevant with δ 208.7 (C-1), show that C-7 ' is connected on the C-2, this can pass through δ 3.31 (H-7 ') and δ 36.7 (C-3), δ 2.50 (H-3), the long-range relevant conclusive evidence that obtains of δ 2.57 (H-3) and δ 40.3 (C-7 ').Substituting group from the phenyl ring has two hydroxyls on the Tetralone an intermediate of Sertraline, lay respectively at C-4 and C-8, and two vicinal hydroxyl groups are arranged on another phenyl ring, and two Sauerstoffatoms are still arranged in the molecular formula, in conjunction with
13C-NMR composes (δ 176.9) data, and showing has a carboxyl to exist, and it can only be connected on the C-8 '.Therefore, Exocarpium Juglandis Immaturum plain A
1H-NMR and
13The C-NMR data are arranged as table 1.From HMBC spectrum (accompanying drawing 2), the structure of this compound has obtained conclusive evidence.
The plain A's of table 1 Exocarpium Juglandis Immaturum
1H-NMR and
13The C-NMR data
Embodiment 4:
The purposes of antineoplastic novel compound in the described immature exocarp of Juglans mandshurica Maxim in antitumor drug.
The plain A of Exocarpium Juglandis Immaturum suppresses people HL-60 leukemia cell, people Kato-III stomach cancer cell and people A
549The activity experiment of lung carcinoma cell:
Cell cultures: people HL-60 leukemia cell, people Kato-III stomach cancer cell and people A
549Lung carcinoma cell is incubated at RPMI 1640 substratum, adds 10% FBS, L-glutamine, 100U/ml penicillin and 100 μ g/ml Streptomycin sulphates.The cell counting of taking the logarithm vegetative period is with 3 * 10
4The concentration of individual/ml is inoculated in 96 orifice plates, and every hole 180 μ l are at 37 ℃, 5% CO
2Incubator in cultivated 24 hours.
Cell toxicant is measured: the medicine of different concns (1-100 μ M) is with EtOH-H
2O (1:9) is dissolution with solvents to 20 μ l, and blank group adds the EtOH-H of 20 μ l
2O (1:9) solution, cell continue to cultivate 72 hours, adopt mtt assay to measure then, and the cell after promptly cultivating adds 10 μ l MTT (5mg/ml) phosphate buffered saline buffers, 37 ℃, 5% CO
2Cultivated 4 hours in the incubator, centrifugal, get supernatant liquor 150 μ l and discard, add 175 μ l DMSO, jolting was measured light absorption value with microplate reader at 550nm after 10 minutes.Calculate according to following formula, draw IC
50
Control wells: only add cell and do not add medicine
Blank well: only solubilizing agent does not add cell and medicine
Experimental port: add cell and add medicine again
Test-results
See Table 2.The result shows, the plain A of Exocarpium Juglandis Immaturum all has in various degree restraining effect to three kinds of tumour cells.
The plain A of table 2. Exocarpium Juglandis Immaturum suppresses the IC of three kinds of tumour cells
50(μ M) value
Annotate: each numerical value is the mean value ± standard deviation of three independent experiments
Embodiment 5:
The content assaying method that the present invention sets up is determined by following experiment:
1. instrument and equipment
Agilent 1100 type high performance liquid chromatographs, quaternary gradient pump, online de-aerator, automatic sampler, column oven, DAD detector; YMC-Pack C18 (4.6 * 150mm) chromatographic columns.
Reagent: methyl alcohol (chromatographically pure, Dikma company), Glacial acetic acid (analytical pure), methyl alcohol (analytical pure).
Medicinal material: Exocarpium Juglandis Immaturum is adopted in 5 constant virtues, Heilongjiang Province county, through being processed into.
Chromatographic condition: with octadecylsilane chemically bonded silica is weighting agent; Moving phase: 0.25% Glacial acetic acid (V/V): methyl alcohol (25:75); The detection wavelength is 350nm; 30 ℃ of column temperatures.
3. the investigation of linearity range
Precision is measured reference substance solution 0.5ml, 1.0ml, 2.0ml, 3.0ml, 4.0ml, the 5.0ml that concentration is 1.20144mg/ml, put respectively in the 10ml measuring bottle, add methyl alcohol to scale, be mixed with the reference substance solution that concentration is respectively 0.060072mg/ml, 0.120144mg/ml, 0.180216mg/ml, 0.240288mg/ml, 0.360432mg/ml, 0.480576mg/ml.Precision is measured each 10 μ l sample introduction of above-mentioned 6 kinds of solution, and the record color atlas is measured its peak area, the results are shown in Table 3.And with peak area value (A) to sample size (C) return the typical curve equation.And with peak area value (A) to sample size (C) mapping, a straight line.
The plain A reference substance of table 3 Exocarpium Juglandis Immaturum measurement result
A＝615917.8C-8.22647，r＝0.9997
The result of accompanying drawing 3 shows that in 0.60072～4.80576 μ g scope, reference substance peak area value and sample size have good linear relationship.
4. the preparation of need testing solution: the method that has adopted different solvents such as 30% methyl alcohol, 50% methyl alcohol, 70% methyl alcohol and methyl alcohol to extract.The plain A content of the Exocarpium Juglandis Immaturum of 50% methanol extraction is maximum and impurity is less as a result, so employing 50% methyl alcohol is the extraction solvent of sample test liquid.
The different investigations of extracting solvent of table 4
5. precision test: accurate reference substance solution (0.20024mg/ml) the 10 μ l that draw, repeat sample introduction 5 times, RSD＜3% of the plain A peak area value of Exocarpium Juglandis Immaturum the results are shown in Table 5, shows that precision is good.
Table 5 Precision test result
6. stability test: the sample thief test liquid was respectively at 0 hour, 2 hours, 4 hours, 8 hours, 16 hours sample introduction 10 μ l, the RSD that records the plain A peak area value of Exocarpium Juglandis Immaturum in the sample is less than 3%, the results are shown in Table 6, show that the sample test liquid is good at 16 hours internal stabilities.
Table 6 stability test result
7. circulation ratio test: press content assaying method, the sample of getting with once collection prepares 5 duplicate samples test liquids respectively, records peak area value and calculates content, and RSD the results are shown in Table 7 less than 3%, shows that circulation ratio is good.
Table 7 reproducible test results (n=2)
8. recovery test: each the about 0.5g of sample that gets 6 parts of known content, add the reference substance solution 3.4ml that concentration is 0.20024mg/ml (100%), 4.1ml (120%) respectively, by sample preparation methods and chromatographic condition in the invention, the preparation application of sample reclaims need testing solution and injects high performance liquid chromatograph, with following formula calculate recovery rate, the results are shown in Table 8.
Table 8 recovery test result
Test-results shows: the rate of recovery is between 95%～105%, and application of sample reclaims good.
Claims (4)
1. the antineoplastic novel compound in the immature exocarp of Juglans mandshurica Maxim, the plain A of called after Exocarpium Juglandis Immaturum, it is characterized in that: described All new compounds formula is:
2. the content assaying method of antineoplastic novel compound in the described immature exocarp of Juglans mandshurica Maxim of claim 1, it is characterized in that: adopt the HPLC method to measure, get the plain A reference substance of Exocarpium Juglandis Immaturum, the accurate title, decide, and adds methyl alcohol and make the solution that every 1ml contains 0.2mg, product solution in contrast, got the immature exocarp of Juglans mandshurica Maxim powder 1g of No. three sieves, the accurate title, decide, and adds 50% methyl alcohol supersound process 30 minutes, put cold, claim again to decide weight, supply the weight that subtracts mistake, shake up with 50% methyl alcohol, filter, as need testing solution, accurate respectively reference substance solution and each 10 μ l of need testing solution of drawing inject liquid chromatograph, measure, promptly.
3. the content assaying method of the antineoplastic novel compound in a kind of immature exocarp of Juglans mandshurica Maxim according to claim 2, it is characterized in that: adopt the HPLC method to measure, be meant that chromatographic condition is to adopt octadecylsilane chemically bonded silica as weighting agent, moving phase is that the volume ratio of 0.25% Glacial acetic acid (V/V) and methyl alcohol is 25: 75, the detection wavelength is 350nm, column temperature is 30 ℃, and number of theoretical plate calculates by the plain A of Exocarpium Juglandis Immaturum peak and is not less than 3000.
4. the application of the antineoplastic novel compound in the described immature exocarp of Juglans mandshurica Maxim in the preparation antitumor drug.
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| CN103217491B (en) * | 2013-03-21 | 2014-07-23 | 黑龙江大学 | Method for establishing high performance liquid chromatography fingerprint spectrum of Exocarpium Juglandis Immaturum antioxidant active extract, its standard fingerprint spectrum and use |
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